DOI: https://doi.org/10.24820/ark.5550190.p011.457 Page 79
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AUTHOR(S)
The Free Internet Journal
for Organic Chemistry
Paper
Archive for
Organic Chemistry
Arkivoc 2020, part iv, 79-85
Ligand exchange of aryl iodine dicarboxylates to form reagents with differing
solubilities
Vanie Seecharan, Lyse Armand, Jennifer Noorollah, Nirvanie Singh, Andrew Zhang, Kevin P. Freddo, Nicholas
Spatola, Sailesh Prasad, Azka Chaudhry, Su Wint War, I. F. Dempsey Hyatt,* and Daniel L. Silverio*
Department of Chemistry, Adelphi University, One South Avenue, Garden City, NY, 11530, United States of
America
Email: dsilverio@adelphi.edu
Received 12-19-2020 Accepted 03-27-2021 Published on line 04-07-2021
Abstract
Hypervalent iodine (HVI) reagents are employed in organic synthesis as versatile, proficient, and
environmentally friendly reagents. Despite the utility of such reagents, the application of HVI reagents,
especially phenyliodonium diacetate (PIDA), has been limited due to its poor solubility in a myriad of solvents.
The aggregated and polymeric structures of many HVI reagents account for their poor solubility, thus limiting
the reactivity and use of HVI reagents in reactions in non-polar solvents. The research presented herein outlines
ligand exchange reactions of universal carboxylic acids promoted by phenyliodonium diacetate (PIDA) reagents,
in which the acetate moiety of PIDA is modified, ultimately enhancing the solubility and reactivity of HVI
reagents.
Keywords: Hypervalent iodine, solubility, PIDA, ligand-exchange